supplementary materials

The title compound, C22H20BrN5OS, is a potent new fungicide. The planes of the phenyl and pyrozole rings are almost perpendicular, making a dihedral angle of 86.5 (4)°. There are two non-classical intermolecular C-HO and C-HN hydrogen bonds in the crystal structure.

A variety of pyrazole and triazole heterocyclics could exhibit many activities.
Meanwhile, heterocyclic compounds is an important developmental direction in
medical (Gong et al., 2008) and pesticidal (Liu et al.,
2007)
chemistry.

In view of these facts and in continuation of our interest in the
agriculture, we attempted to synthesize a series of amide derivatives, some of
which have comparatively high fungicidal activity.

The molecular structure of title compound is showing in Fig.1. The x-ray
analysis reveals that acetyl group is a planar with thio-ether group. The
pyrozole ring is vertical with the benzene ring [dihedral angle 93.5 (4)°].
The packing of the structure is due to the weak intermolecular C-H..O and
C-H..N H-bonds (Table 1. and Fig 2.).

The compound
5-((3,5-Dimethyl-1H-pyrazol-1-yl)methyl)-4-phenyl-4H-1,2,4
-triazole-3-thiol was synthesized according to the reference (He et al.,
2008). Then added p-bromo-phenacyl bromide, potassium carbonate
anhydrous and N,N-Dimethyl formamide was stirred at room
temperature for 5 h, giving the title compound. Colorless single crystals
suitable for x-ray diffraction were obtained by recrystallization from a
mixture of ethyl acetate and petroleum ether.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.